Cyclopentanone → Pyrrolidine, 1-(1-cyclopenten-1-yl)-

HRID 2249888Notes

Reaction equation

HRID 2249888 reaction equation
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1>C1(C)C=CC=CC=1>[C:1]1([N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)[CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

4

Reactant 2

HCID 8452CyclopentanoneHCID 31268Pyrrolidine

Product 1

HCID 81570Pyrrolidine, 1-(1-cyclopenten-1-yl)-Yield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of cyclopentanone (25.0 mL, 0.28 mol, 1.0 eq.) in toluene (100 mL), was added pyrrolidine (27.5 mL, 1.2 eq.). The reaction was equipped with a Dean-Stark and heated at reflux overnight. The reaction mixture was cooled to room temperature and concentrated to give the crude 1-cyclopent-1-enyl-pyrrolidine (45.8 g, >100%).

Workup

  1. customThe reaction was equipped with a Dean-Stark
  2. temperatureheated
  3. temperatureat reflux overnight
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-64a8b1c3a1d04c078553ee34f8037f8b
Source dataset
uspto-grants-2008_01
Patent number
US07314936B2

Reaction notes

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